Paul Simon’s 10 best songs

By Sergio Ariza

Paul Simon is one of the great composers of the last century, someone who began by emulating his beloved Everly Brothers, became a folk troubadour and found success by chance with folk rock. But Simon has always been a freelancer and has had his ears wide open to a lot of music, as shown by the enormous success he had in his solo career with his approaches to African or Brazilian music. But whether he drew on folk or reggae, gospel or pop, what was always clear was the quality of his compositions, something that has made of him one of the most covered songwriters in history. Here are our 10 favorites from his excellent catalog. 

Mrs. Robinson

After recording the splendid album Parsley, Sage, Rosemary & Thyme, Simon had writers’ block. Around the same time the director Mike Nichols, who was preparing The Graduate, became obsessed with his music, especially with that album and the prior one, Sounds Of Silence. He asked the record company's boss for permission to use Simon's songs, but the boss, Clive Davis, decided it was a good opportunity to record a new album, so he put Simon in touch with Nichols; they got along well and Simon started writing again. The first two songs by Simon didn't particularly please him but soon after Simon wrote Mrs. Robinson; the song still didn't have all the lyrics and Simon and his partner Garfunkel completed it with those "dee de dee de dee dee" that made Nichols very excited. The song was still not finished but was nonetheless used in the movie, in a kind of demo format. Simon & Garfunkel finished recording it on February 2, 1968 and it was released in April, three months after the film appeared. It was perfect for the promotion of the film, and climbed to the top of the US charts. This is understandable if we consider the glorious melody, the accurate lyrics that summarized the times, the excellent contribution of Hal Blaine on drums and Larry Knechtel on bass, as well as the great work of Simon on his F-30 Guild guitar.

A great cover: The Lemonheads



Recorded the day before Mrs. Robinson, America was further proof that Simon had ended his creative drought for good. This melancholy wonder was based on a five-day hitchhiking trip that Simon took in 1964 with his girlfriend at the time, Kathy Chitty, a person who also appears in other songs of his such as Homeward Bound and Kathy's Song. The song appeared in the outstanding Bookends and was chosen by the Swedish duo First Aid Kit as a tribute to Simon when he won the Polar Music Prize, which earned them a well-deserved standing ovation from the composer.

A great cover: First Aid Kit 


Bridge Over Troubled Water

An enormous song that spoke of an indestructible friendship at a time when, ironically, Simon's friendship with Art Garfunkel was leaking all over the place. The curious thing is that, at a time like this, Simon decided to give the lead vocal on the song to Garfunkel, something he would regret. But at an artistic level it was an absolute success, Garfunkel's sweet choirboy voice was a perfect match for an imperishable melody that at times sounded like Bach and at others like gospel. The mythical Hal Blaine of the Wrecking Crew added his drums to it (we are talking about the drummer who has recorded the most number one hits in history) and Larry Knechtel the keyboard, which sounded like a church organ. Perhaps we can appreciate the songs greatness if we think of some of the artists who have recorded a cover version of it, Elvis Presley, Aretha Franklin, Johnny Cash with Fiona Apple, Willie Nelson, the Jackson 5, the Supremes or Roberta Flack.

A great cover: Elvis Presley


Homeward Bound

Paul Simon and Art Garfunkel released their debut album in October 1964 but it went nowhere. Simon had started dating Kathy Chitty but decided to move to London to find a way out. It was there, at Liverpool station, where he started writing this song full of nostalgia for his home and his girl. He was still in Europe when he learned that his song, The Sound Of Silence, had become a hit after producer Tom Wilson added electric guitar, bass and drums, inspired by the success of the Byrds. Simon rushed back to the US and rejoined Garfunkel to record something in the same style. Simon carried Homeward Bound with him and the duo recorded it, with bass and drums already in the mix, in December 1965. It went on sale the following month and becoming a success on its own, reaching number five in the charts.
 A great cover: Willie Nelson


The Only Living Boy In New York

Simon & Garfunkel’s separation actualy became a song! Simon felt alone in New York while Garfunkel (Tom, a reference to their beginnings when they called themselves Tom & Jerry) went to Mexico to act in a movie. Simon once again took advantage of his loneliness and sadness to deliver one of the best songs from the band's last album, Bridge Over Troubled Water. The usual session musicians, Blaine, Knechtel on the organ and Joe Osborn on the bass are back, while Simon uses a 12-string Guild. The wonderful background vocals were recorded by the duo in an echo chamber to achieve that particular effect.

A great cover: Everything But The Girl


The Sound Of Silence

This was the song that gave Simon ‘rocambolesque success’. Simon and Garfunkel recorded the original version of the song on March 10, 1964, and it appeared on the band's first album, Wednesday Morning, 3 A.M., in October of that same year without being noticed. But in April 1965, the Byrds' Mr. Tambourine Man became a huge success and unleashed folk rock fever. Shortly thereafter, Wednesday Morning's producer, Tom Wilson, who had worked with
Dylan on Highway 61 Revisited, decided to call in a few session musicians and add guitar, bass and drums to the song. Musician Al Gorgini says he followed Simon's guitar but that everyone was thinking of the Byrds when they recorded it, though it wasn't with a Rickenbacker but with an Epiphone Casino.

A great cover: Marie Laforêt


A Hazy Shade Of Winter

The most rocking song of Simon's career came out as a single in 1966 but was revived for Bookends two years later. Here Simon gives away a wonderful riff, (made with his acoustic Guild but perfect for an electric one, as the Bangles would show years later) and even allows Blaine to get a little wild on the drums. Another unusual thing is the arrangements with trumpet included.

A great cover: The Bangles


I Am A Rock

While in England Paul Simon recorded an album entitled The Paul Simon Songbook, which was released in August 1965. There was already an acoustic version of that gem called I Am a Rock. It was another of the songs that he recovered after the unexpected success of The Sound Of Silence, recording it on December 14, 1965 and releasing it in May 1966. It was the third success in a row by the duo, rising to number three in the charts. In the song, the feeling of isolation felt by Simon is again appreciated, as he affirms, at the end of the song, "I am a rock, I am an island, and a rock feels no pain, and an island never cries". Musically it is the most folk rock song of his career, with Glen Campbell's jangling Teisco T-60, joined by the band's usual suspects, Blaine, Knechtel and Osborn.

A great cover: The Hollies



We make a leap of several years and go to the best album of his remarkable solo career (a stage from which other great songs could have been chosen, such as Me and Julio Down By The Schoolyard, 50 Ways To Leave Your Lover or American Tune): Graceland, released in 1986. The album reflected Simon's fascination with African music, particularly South African; the kind of sound that reminded him of the origins of rockabilly on Sun Records. Not surprisingly, the title track revolves around a trip to Graceland, King Elvis' Camelot, and it is accompanied by his revered Everly Brothers on vocals. The song benefited from the excellent work of South African guitarist Chikapa 'Ray' Phiri, whose Stratocaster is capable of bringing out the purest and most liquid sounds, and Demola Adepoju on steel pedal.

A great cover: Justin Townes Earle


The Dangling Conversation

This is one of Simon's favorite songs, also composed in 1966, which was chosen as the first single from Parsley, Sage, Rosemary & Thyme. However when it did not achieve the same success as the songs that preceded it, its author was amazed because he thought it was the best thing he had done to date. Perhaps the lyrics, full of literary references to Emily Dickinson and Robert Frost, about a couple disintegrating, were the reason, because both the melody and the string arrangement were absolutely brilliant.

A great cover: Joan Baez